Heterocyclic azide units and their use in polymer coatings

Abstract

Described herein are heterocyclic azide-containing monomer units, copolymers comprising such heterocyclic azide-containing monomer units, substrate-bound copolymers, and oligonucleotide-bound copolymers, methods for making such copolymers and reacting them with a substrate and/or oligonucleotide, and methods of using such copolymers for immobilization of oligonucleotides to a substrate, for example for use in DNA sequencing or other diagnostic applications.

What is claimed is: 
     
       1. A compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H or C 1-4  alkyl; 
         R 2  is H or C 1-4  alkyl; 
         L is a linker comprising a linear chain having 2 to 20 atoms selected from the group consisting of carbon, oxygen, and nitrogen and optional substituents on the carbon and any nitrogen atoms in the chain; 
         E is a linear chain having 1 to 4 atoms selected from the group consisting of carbon, oxygen and nitrogen, and optional substituents on the carbon and any nitrogen atoms in the chain; 
         A is an N substituted amide having formula 
       
       
         
           
           
               
               
           
         
          wherein R 3  is H or C 1-4  alkyl; and 
         Z is a nitrogen containing heterocycle. 
       
     
     
       2. The compound according to  claim 1 , wherein E is optionally substituted C 1-4  alkylene. 
     
     
       3. The compound according to  claim 1 , wherein the compound is of formula (Ia) 
       
         
           
           
               
               
           
         
         wherein p is 1, 2, 3 or 4. 
       
     
     
       4. The compound according to  claim 1 , wherein the nitrogen containing heterocycle comprises a 6 membered ring. 
     
     
       5. The compound according to  claim 4 , wherein A and E are bonded at positions 2 and 5 of the 6 membered ring. 
     
     
       6. The compound according to  claim 1 , wherein the nitrogen containing heterocycle comprises a 5 membered ring. 
     
     
       7. The compound according to  claim 1 , wherein the nitrogen containing heterocycle is aromatic. 
     
     
       8. The compound according to  claim 1 , wherein the nitrogen containing heterocycle is saturated. 
     
     
       9. The compound according to  claim 1 , wherein the compound is of formula (Ib) 
       
         
           
           
               
               
           
         
         wherein X is CH or N; and 
         wherein p is 1, 2, 3 or 4. 
       
     
     
       10. The compound according to  claim 1 , wherein the compound is of formula (Ic) 
       
         
           
           
               
               
           
         
         wherein p is 1, 2, 3 or 4. 
       
     
     
       11. The compound according to  claim 1 , wherein the compound is of formula (Id) 
       
         
           
           
               
               
           
         
         wherein p is 1, 2, 3 or 4. 
       
     
     
       12. The compound according to  claim 1 , wherein the compound is of formula (Ie) 
       
         
           
           
               
               
           
         
         wherein p is 1, 2, 3 or 4. 
       
     
     
       13. The compound according to  claim 1 , wherein the compound is of formula (If) 
       
         
           
           
               
               
           
         
       
     
     
       14. The compound according to  claim 1 , wherein the compound is of formula (Ig) 
       
         
           
           
               
               
           
         
       
     
     
       15. The compound according to  claim 1 , wherein the compound is of formula (Ih) 
       
         
           
           
               
               
           
         
       
     
     
       16. The compound according to  claim 1 , wherein the compound is of formula (Ij) 
       
         
           
           
               
               
           
         
       
     
     
       17. The compound according to  claim 1 , wherein the compound of formula (Ik): 
       
         
           
           
               
               
           
         
         wherein X is CH or N; and 
         wherein p is 1, 2, 3 or 4. 
       
     
     
       18. The compound according to  claim 17 , wherein the compound of Formula (Ik) is a compound of Formula (Im): 
       
         
           
           
               
               
           
         
         wherein n is an integer from 2 to 20; and 
         wherein p is 1, 2, 3 or 4. 
       
     
     
       19. A copolymer comprising a recurring monomer unit of formula (II): 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H or C 1-4  alkyl; 
         R 2  is H or C 1-4  alkyl; 
         L is a linker comprising a linear chain having 2 to 20 atoms selected from the group consisting of carbon, oxygen, and nitrogen and optional substituents on the carbon and any nitrogen atoms in the chain; 
         E is a linear chain having 1 to 4 atoms selected from the group consisting of carbon, oxygen and nitrogen, and optional substituents on the carbon and any nitrogen atoms in the chain; 
         A is an N substituted amide having formula 
       
       
         
           
           
               
               
           
         
          wherein R 3  is H or C 1-4  alkyl; and 
         Z is a nitrogen containing heterocycle; and 
         at least one other recurring monomer unit. 
       
     
     
       20. The copolymer according to  claim 19 , wherein the recurring monomer unit of formula (II) is a recurring monomer unit of formula (IIa) 
       
         
           
           
               
               
           
         
         where p is 1, 2, 3, or 4.